sincerely; earnestly; wholeheartedly
Used to emphasize a heartfelt request, warning, or expression of concern. Often appears in polite requests or when urging someone to take care.
くれぐれもお体に気をつけてください。
Please take good care of yourself.
Please don't overdo it, I sincerely mean it.
repeatedly; over and over; again and again
Rare, somewhat archaic use meaning 'repeatedly' or 'over and over'. In modern Japanese, the first sense (sincere request) is overwhelmingly more common.
In old letters, くれぐれも was sometimes used to mean 'repeatedly' as in 'I say again and again'.
I sincerely ask for your continued support.
Please be sure to take care not to catch a cold.
Please give my warmest regards to your family.
The stairs are slippery, so please be extremely careful.